A reader asked me about the mechanism of the reaction of 2-picoline N-oxide with acetic anhydride to give 2-acetoxymethylpyridine (the Boekelheide Rearrangement[cite]10.1002/ejoc.201000936[/cite]). He wrote ” I don’t understand why the system should prefer to go via fragmentation-recombination (… the evidence being that oxygen labelling shows scrambling) when there is an easy concerted pathway available (… a
AbstractPyrrolidines and piperidines were synthesized from (aminoalkyl)pyridine N‐oxides with a general and quite efficient method developed by using di‐tert‐butylsilyl bis(trifluoromethanesulfonate) as a new promoter for a Boekelheide‐type reaction. The use of a new Boekelheide promoter, which is compatible with amino groups, opens new perspectives in view of its application in intramolecular cyclizations.
Archive of work produced using the resources of the Imperial College High Performance Computing Service.
Archive of work produced using the resources of the Imperial College High Performance Computing Service.
Archive of work produced using the resources of the Imperial College High Performance Computing Service.